Holiday rentals with outdoor seating in Poughkeepsie

Slate Cabin - Stylish Country Escape x Rhinebeck

This designer cabin blends natural materials and modern finishes. — sophisticated & cozy. Gaze at (or swim in!) the stunning spring-fed pond steps from the house. Lounge on the deck or enjoy coffee in the sunroom. The interiors feature three bedrooms, two full bathrooms, living room with chic and cozy furniture and wood burning fireplace, and fully appointed kitchen that's a joy to cook in. Entertain your family & friends at the table for 10 and continue out to the grounds, beverage in hand.

The Cozy Cape In Historic Hyde Park

Modern amenities meets early 20th century charm in our cozy, totally renovated space situated in the hearth of the historic town of Hyde Park and adjacent to the Hudson River. Built in the 1940s, our Cozy Cape is nestled in a quiet neighborhood off of Route 9 & is central to historic sites, shopping, parks, and dining options. Our home is also minutes by car to the Culinary Institute Of America, Walkway Over The Hudson, wineries, antique shops, Marist and Vassar colleges & Town of Rhinebeck!

Boulder Tree House

Boulder Tree House 🌲🌲🌲 FRESH AIR • SMOKE FREE • ALLERGY FREE Early Check In & Late Check Out! Boulder Tree House is an Inhabitable Work of Art, created by owner architects. The design is based on organic and innovative blending of natural elements and environmentally conscious technology, creating a happy and healthy living space. Boulder Tree House is ideal for a couple looking for a exciting, romantic and unique experience. The space can also comfortably accommodate a 3rd person.

Tranquil Tree-House on the beautiful Hudson River

Take it easy at this unique and tranquil getaway. I look forward to hosting you. Enjoy a private room with a queen size bed and a large screen smart tv. The full bathroom is located across the hallway. Enjoy a warm fire in the sitting area. There is a work area and a high table to enjoy some tea/coffee or wine with dinner while enjoying the view of the Hudson through the large windows and sliding door. We have added a separate kitchenette additional crockpot and induction cooktop.

Under the walkway near the train in Little Italy

Beautiful downtown apartment under the walkway over the Hudson. It sits on one of the nicest streets in a safe neighborhood within walking distance to the metro north train station (3 blocks), restaurants (across street from Farmers and Chefs), bars and bakeries. The walkway is also near by. Outdoor back patio and fire pit are exclusive for this listing. There is also a studio below that can be rented which will give you the entire building. Be mindful of the guests staying down stairs.a

3Br Hilltop Ranch on 130acre farm w/ falls & creek

Newly renovated ranch house on a private hill top of an 130 acre magical property with stunning eastern views and overlooking a historic farm. Explore the hiking trails, dip in the wading pools of 90ft waterfall's upper cascades, bike to town or simply relax on the hammock while taking in views of the rolling hills. Escape to a beautifully designed private retreat, complete with a gourmet kitchen, cozy fireplaces, and comfortable bedrooms with quiet workspaces- learn more at cascadafarm

Cliff Top at Turtle Rock

Cliff Top retreat with a one hundred mile view of the Shawangunk's and the Catskill Mountains, surrounded by thousands of acres of ancient forest. Conveniently located in the Hudson Valley Wine and Orchard country. Twenty minutes from Beacon and New Paltz. Furnished with mid-century and 18th century period furniture and art work, yet with all the modern conveniences. Uber and Lift an easy five minutes away. The ancient forest contains many Stone Age rock shelters and calendar sites.

Hillside Views in Hudson Valley

Escape to this modern, cozy retreat where nature surrounds you. Fall asleep to owls, crickets, and frogs. Just 2 mins from Rosendale and a short drive to Kingston, New Paltz, and Stone Ridge, with restaurants and trails nearby. Enjoy a gas fireplace, a reading nook with treetop views, and a large deck that feels like you’re in the trees. The private outdoor space includes a fire pit, all on a serene 3-acre lot offering total peace and quiet. Your perfect Hudson Valley escape awaits!

The Hudsy Home

Welcome to our cozy retreat nestled in the heart of the Hudson Valley! Your escape awaits with a personal entrance to this cozy apartment inside our home. Unwind in the spacious bedroom, perfect for a couple's night's sleep. The living area features a 65-inch flat-screen TV for your enjoyment. Walkway Over The hudson is just a short 5-minute stroll away. For your convenience, you're only moments away from local favorites like Starbucks, Chipotle, CVS, Shoprite and more :)

Suite of Rooms in Historic Home

Wonderfully decorated 3rd floor suite of rooms in the Academy Historic District. Two Newly renovated bedrooms, one with queen bed, the other with 2 twin beds. There is an additional day bed in the living area/ sitting room space , a TV with Netflix & Amazon Prime with wifi connection throughout. The bathroom has modern fixtures and a claw-foot tub/shower. There is a private entrance with additional half bath . A private porch and use of the beautiful backyard.

4BR|2Bath|King Beds|Walk to Marist|CIA|Pet|Parking

This home is located in the Mid Hudson Valley -just steps away from Marist U, The entrance to Walkway Over the Hudson, MHR Hospital and a 2mi ride to the CIA! Equipped with a full kitchen, king beds, 2 full baths, Roku TV, private parking & spacious backyard- perfect for grilling or cozying up next to the fire pit. Make this cheerful house your home base as you explore all the wonders of the Hudson Valley! We are a small dog friendly! (15 lbs or less)

Modern/lux suite on Hudson Riverfront w/views!

Come stay on the Hudson River Waterfront Bluff! It is one of THE most magical, luxurious experiences in all of NY. The views are insane!! It's literally the perfect getaway with a major *wow* factor - if you're wanting something very special. :) You'll have complete access to my gorgeous, modern, designer 2-room guest suite. The entrance is separate/private. This is a luxury escape. The central location positions you near everything!